A Novel Highly Stereoselective Synthesis of 2,3-Disubstituted 3H-Quinazoline-4-one Derivatives
Organic Letters2007Vol. 9(7), pp. 1415–1418
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Paul Zhichkin, Edward A. Kesicki, Jennifer Treiberg, Lisa H. Bourdon, Matthew D. Ronsheim, Hua Chee Ooi, Stephen White, Angela Judkins, David J. Fairfax
Abstract
[structure: see text]. An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee >93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.
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